# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA244
_database_code_depnum_ccdc_archive 'CCDC 1831968'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        N10TM
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H29 N O4'
_chemical_formula_sum            'C14 H29 N O4'
_chemical_formula_weight         275.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0074 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.667(4)
_cell_length_b                   8.6810(17)
_cell_length_c                   9.0510(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.06(3)
_cell_angle_gamma                90
_cell_volume                     1623.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    35761
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15466
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4509
_reflns_number_gt                2684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.134(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4509
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07946(6) 0.50027(15) -0.00073(12) 0.0593(4) Uani 1 1 d . . . . .
H1 H 0.107101 0.435710 -0.019355 0.089 Uiso 1 1 calc R U . . .
O2 O -0.01921(5) 0.43440(14) 0.26112(11) 0.0473(3) Uani 1 1 d . . . . .
H2 H -0.031361 0.442098 0.174678 0.071 Uiso 1 1 calc R U . . .
O3 O 0.11135(8) 0.4926(2) 0.53348(13) 0.0822(5) Uani 1 1 d . . . . .
H3 H 0.083041 0.508089 0.594030 0.123 Uiso 1 1 calc R U . . .
O4 O 0.18204(5) 0.33307(12) 0.04214(11) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.15739(5) 0.37508(13) 0.28223(12) 0.0349(3) Uani 1 1 d . . . . .
H1H H 0.171451 0.359308 0.370963 0.042 Uiso 1 1 calc R U . . .
C1 C 0.09835(6) 0.47001(14) 0.26813(14) 0.0319(3) Uani 1 1 d . . . . .
C2 C 0.09599(7) 0.57526(16) 0.13261(16) 0.0426(3) Uani 1 1 d . . . . .
H2A H 0.064760 0.656499 0.149483 0.051 Uiso 1 1 calc R U . . .
H2AB H 0.138026 0.623353 0.122217 0.051 Uiso 1 1 calc R U . . .
C3 C 0.04128(7) 0.35867(16) 0.26769(17) 0.0412(3) Uani 1 1 d . . . . .
H3A H 0.044519 0.290237 0.183426 0.049 Uiso 1 1 calc R U . . .
H3AB H 0.043621 0.296161 0.356458 0.049 Uiso 1 1 calc R U . . .
C4 C 0.09695(8) 0.57535(19) 0.40350(16) 0.0491(4) Uani 1 1 d . . . . .
H4A H 0.128262 0.657549 0.392198 0.059 Uiso 1 1 calc R U . . .
H4AB H 0.054413 0.621641 0.410802 0.059 Uiso 1 1 calc R U . . .
C5 C 0.19175(6) 0.31065(14) 0.17564(14) 0.0330(3) Uani 1 1 d . . . . .
C6 C 0.24750(7) 0.20915(16) 0.22494(16) 0.0405(3) Uani 1 1 d . . . . .
H6A H 0.255967 0.133547 0.148781 0.049 Uiso 1 1 calc R U . . .
H6AB H 0.235811 0.154279 0.313909 0.049 Uiso 1 1 calc R U . . .
C7 C 0.30807(8) 0.30241(19) 0.2551(2) 0.0592(5) Uani 1 1 d . . . . .
H7A H 0.299840 0.374093 0.334802 0.071 Uiso 1 1 calc R U . . .
H7AB H 0.317717 0.362330 0.167781 0.071 Uiso 1 1 calc R U . . .
C8 C 0.36669(7) 0.2060(2) 0.2964(2) 0.0552(4) Uani 1 1 d . . . . .
H8A H 0.356561 0.144012 0.382024 0.066 Uiso 1 1 calc R U . . .
H8AB H 0.375530 0.136219 0.215515 0.066 Uiso 1 1 calc R U . . .
C9 C 0.42679(9) 0.2982(2) 0.3305(3) 0.0705(6) Uani 1 1 d . . . . .
H9A H 0.417985 0.366221 0.412684 0.085 Uiso 1 1 calc R U . . .
H9AB H 0.435944 0.362350 0.245625 0.085 Uiso 1 1 calc R U . . .
C10 C 0.48653(8) 0.2055(2) 0.3683(2) 0.0654(5) Uani 1 1 d . . . . .
H10A H 0.477471 0.141528 0.453268 0.079 Uiso 1 1 calc R U . . .
H10B H 0.495354 0.137351 0.286133 0.079 Uiso 1 1 calc R U . . .
C11 C 0.54616(9) 0.2978(2) 0.4018(3) 0.0751(6) Uani 1 1 d . . . . .
H11A H 0.554569 0.362902 0.317160 0.090 Uiso 1 1 calc R U . . .
H11B H 0.537207 0.365126 0.484438 0.090 Uiso 1 1 calc R U . . .
C12 C 0.60646(9) 0.2095(2) 0.4379(3) 0.0756(6) Uani 1 1 d . . . . .
H12A H 0.598375 0.145556 0.523478 0.091 Uiso 1 1 calc R U . . .
H12B H 0.615183 0.141055 0.355850 0.091 Uiso 1 1 calc R U . . .
C13 C 0.66549(10) 0.3023(3) 0.4688(3) 0.0997(9) Uani 1 1 d . . . . .
H13A H 0.672540 0.368826 0.384502 0.120 Uiso 1 1 calc R U . . .
H13B H 0.657094 0.368211 0.552811 0.120 Uiso 1 1 calc R U . . .
C14 C 0.72624(12) 0.2166(4) 0.5000(5) 0.1414(14) Uani 1 1 d . . . . .
H14A H 0.736054 0.152292 0.417084 0.212 Uiso 1 1 calc R U . . .
H14B H 0.721043 0.153721 0.586226 0.212 Uiso 1 1 calc R U . . .
H14C H 0.760966 0.288264 0.516913 0.212 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4078(18) . ?
O1 H1 0.8200 . ?
O2 C3 1.4128(17) . ?
O2 H2 0.8200 . ?
O3 C4 1.405(2) . ?
O3 H3 0.8200 . ?
O4 C5 1.2366(16) . ?
N1 C5 1.3316(17) . ?
N1 C1 1.4759(16) . ?
N1 H1H 0.8600 . ?
C1 C3 1.5248(19) . ?
C1 C2 1.5296(18) . ?
C1 C4 1.5296(18) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.5114(18) . ?
C6 C7 1.511(2) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C7 C8 1.513(2) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 C9 1.505(2) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 C10 1.508(2) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C10 C11 1.496(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.494(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.484(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.482(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
C4 O3 H3 109.5 . . ?
C5 N1 C1 128.53(11) . . ?
C5 N1 H1H 115.7 . . ?
C1 N1 H1H 115.7 . . ?
N1 C1 C3 106.53(10) . . ?
N1 C1 C2 114.64(11) . . ?
C3 C1 C2 111.30(11) . . ?
N1 C1 C4 107.00(10) . . ?
C3 C1 C4 110.79(12) . . ?
C2 C1 C4 106.53(12) . . ?
O1 C2 C1 114.51(12) . . ?
O1 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
O1 C2 H2AB 108.6 . . ?
C1 C2 H2AB 108.6 . . ?
H2A C2 H2AB 107.6 . . ?
O2 C3 C1 112.89(11) . . ?
O2 C3 H3A 109.0 . . ?
C1 C3 H3A 109.0 . . ?
O2 C3 H3AB 109.0 . . ?
C1 C3 H3AB 109.0 . . ?
H3A C3 H3AB 107.8 . . ?
O3 C4 C1 111.00(13) . . ?
O3 C4 H4A 109.4 . . ?
C1 C4 H4A 109.4 . . ?
O3 C4 H4AB 109.4 . . ?
C1 C4 H4AB 109.4 . . ?
H4A C4 H4AB 108.0 . . ?
O4 C5 N1 124.25(12) . . ?
O4 C5 C6 119.29(12) . . ?
N1 C5 C6 116.41(11) . . ?
C5 C6 C7 111.43(12) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6AB 109.3 . . ?
C7 C6 H6AB 109.3 . . ?
H6A C6 H6AB 108.0 . . ?
C6 C7 C8 113.89(14) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7AB 108.8 . . ?
C8 C7 H7AB 108.8 . . ?
H7A C7 H7AB 107.7 . . ?
C9 C8 C7 114.25(15) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8AB 108.7 . . ?
C7 C8 H8AB 108.7 . . ?
H8A C8 H8AB 107.6 . . ?
C8 C9 C10 115.62(15) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9AB 108.4 . . ?
C10 C9 H9AB 108.4 . . ?
H9A C9 H9AB 107.4 . . ?
C11 C10 C9 115.36(16) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 116.74(17) . . ?
C12 C11 H11A 108.1 . . ?
C10 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C10 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C13 C12 C11 116.22(18) . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 117.0(2) . . ?
C14 C13 H13A 108.0 . . ?
C12 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
C12 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C3 88.27(16) . . . . ?
C5 N1 C1 C2 -35.30(18) . . . . ?
C5 N1 C1 C4 -153.18(14) . . . . ?
N1 C1 C2 O1 78.15(15) . . . . ?
C3 C1 C2 O1 -42.84(16) . . . . ?
C4 C1 C2 O1 -163.72(12) . . . . ?
N1 C1 C3 O2 177.43(11) . . . . ?
C2 C1 C3 O2 -56.95(15) . . . . ?
C4 C1 C3 O2 61.39(15) . . . . ?
N1 C1 C4 O3 -45.64(17) . . . . ?
C3 C1 C4 O3 70.10(16) . . . . ?
C2 C1 C4 O3 -168.69(13) . . . . ?
C1 N1 C5 O4 7.0(2) . . . . ?
C1 N1 C5 C6 -175.53(12) . . . . ?
O4 C5 C6 C7 92.29(17) . . . . ?
N1 C5 C6 C7 -85.36(16) . . . . ?
C5 C6 C7 C8 -176.62(14) . . . . ?
C6 C7 C8 C9 -178.48(17) . . . . ?
C7 C8 C9 C10 -178.53(19) . . . . ?
C8 C9 C10 C11 179.88(19) . . . . ?
C9 C10 C11 C12 -179.3(2) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C11 C12 C13 C14 -178.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.82 1.86 2.5926(15) 147.6 . yes
O2 H2 O1 0.82 1.91 2.7053(16) 162.2 3_565 yes
O3 H3 O2 0.82 1.94 2.7594(18) 174.3 3_566 yes
N1 H1H O3 0.86 2.26 2.6829(17) 110.2 . yes
N1 H1H O4 0.86 2.29 3.0024(15) 140.9 4_566 yes

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.051

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA245
_database_code_depnum_ccdc_archive 'CCDC 1831969'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        N12TM
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H33 N O4'
_chemical_formula_sum            'C16 H33 N O4'
_chemical_formula_weight         303.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0074 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.076(5)
_cell_length_b                   8.6760(17)
_cell_length_c                   9.0510(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.41(3)
_cell_angle_gamma                90
_cell_volume                     1811.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    284(2)
_cell_measurement_reflns_used    39791
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.057
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      284(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16669
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.792
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4799
_reflns_number_gt                3346
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1155P)²+0.6033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.136(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4799
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.2292
_refine_ls_wR_factor_gt          0.2175
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07089(7) 0.4992(2) 1.00883(16) 0.0566(5) Uani 1 1 d . . . . .
H1O H 0.094801 0.431710 1.027915 0.085 Uiso 1 1 calc R U . . .
O2 O -0.01729(5) 0.43478(18) 0.73657(15) 0.0431(4) Uani 1 1 d . . . . .
H2 H -0.027091 0.447925 0.822123 0.065 Uiso 1 1 calc R U . . .
O3 O 0.09994(9) 0.4934(3) 0.47802(17) 0.0775(7) Uani 1 1 d . . . . .
H3 H 0.075497 0.512426 0.413283 0.116 Uiso 1 1 calc R U . . .
O4 O 0.16308(6) 0.33300(17) 0.97584(14) 0.0440(4) Uani 1 1 d . . . . .
N1 N 0.14102(6) 0.37530(17) 0.73338(15) 0.0305(3) Uani 1 1 d . . . . .
H1 H 0.153722 0.359686 0.646110 0.037 Uiso 1 1 calc R U . . .
C1 C 0.08812(6) 0.47046(19) 0.74141(18) 0.0279(3) Uani 1 1 d . . . . .
C2 C 0.08592(8) 0.5752(2) 0.8772(2) 0.0386(4) Uani 1 1 d . . . . .
H2A H 0.123587 0.623157 0.892165 0.046 Uiso 1 1 calc R U . . .
H2AB H 0.058001 0.656688 0.857431 0.046 Uiso 1 1 calc R U . . .
C3 C 0.03692(7) 0.3585(2) 0.7359(2) 0.0376(4) Uani 1 1 d . . . . .
H3A H 0.039038 0.296176 0.647275 0.045 Uiso 1 1 calc R U . . .
H3AB H 0.039783 0.289939 0.820415 0.045 Uiso 1 1 calc R U . . .
C4 C 0.08710(9) 0.5760(3) 0.6063(2) 0.0444(5) Uani 1 1 d . . . . .
H4A H 0.049070 0.622712 0.594693 0.053 Uiso 1 1 calc R U . . .
H4AB H 0.115257 0.657947 0.620909 0.053 Uiso 1 1 calc R U . . .
C5 C 0.17163(7) 0.31050(19) 0.84343(18) 0.0285(3) Uani 1 1 d . . . . .
C6 C 0.22156(7) 0.2089(2) 0.7988(2) 0.0353(4) Uani 1 1 d . . . . .
H6A H 0.230092 0.135283 0.877050 0.042 Uiso 1 1 calc R U . . .
H6AB H 0.210442 0.151527 0.710577 0.042 Uiso 1 1 calc R U . . .
C7 C 0.27535(9) 0.3026(3) 0.7691(3) 0.0527(6) Uani 1 1 d . . . . .
H7A H 0.267050 0.372104 0.687326 0.063 Uiso 1 1 calc R U . . .
H7AB H 0.284624 0.364959 0.855435 0.063 Uiso 1 1 calc R U . . .
C8 C 0.32768(8) 0.2061(3) 0.7328(3) 0.0496(5) Uani 1 1 d . . . . .
H8A H 0.336413 0.138318 0.815650 0.060 Uiso 1 1 calc R U . . .
H8AB H 0.317943 0.141751 0.648112 0.060 Uiso 1 1 calc R U . . .
C9 C 0.38126(10) 0.2976(3) 0.6993(4) 0.0628(7) Uani 1 1 d . . . . .
H9A H 0.372438 0.364683 0.615944 0.075 Uiso 1 1 calc R U . . .
H9AB H 0.390528 0.362881 0.783600 0.075 Uiso 1 1 calc R U . . .
C10 C 0.43405(9) 0.2043(3) 0.6644(3) 0.0588(7) Uani 1 1 d . . . . .
H10A H 0.442845 0.137141 0.747595 0.071 Uiso 1 1 calc R U . . .
H10B H 0.424833 0.139290 0.579870 0.071 Uiso 1 1 calc R U . . .
C11 C 0.48730(10) 0.2959(3) 0.6314(4) 0.0644(7) Uani 1 1 d . . . . .
H11A H 0.496186 0.361627 0.715617 0.077 Uiso 1 1 calc R U . . .
H11B H 0.478472 0.362499 0.547787 0.077 Uiso 1 1 calc R U . . .
C12 C 0.54066(9) 0.2041(3) 0.5975(3) 0.0620(7) Uani 1 1 d . . . . .
H12A H 0.549483 0.137056 0.680770 0.074 Uiso 1 1 calc R U . . .
H12B H 0.531985 0.138922 0.512723 0.074 Uiso 1 1 calc R U . . .
C13 C 0.59364(10) 0.2972(3) 0.5657(4) 0.0667(8) Uani 1 1 d . . . . .
H13A H 0.584823 0.362885 0.481374 0.080 Uiso 1 1 calc R U . . .
H13B H 0.601621 0.363962 0.649680 0.080 Uiso 1 1 calc R U . . .
C14 C 0.64767(10) 0.2090(3) 0.5343(4) 0.0692(8) Uani 1 1 d . . . . .
H14A H 0.656153 0.141635 0.617632 0.083 Uiso 1 1 calc R U . . .
H14B H 0.640092 0.143986 0.448815 0.083 Uiso 1 1 calc R U . . .
C15 C 0.70029(12) 0.3033(4) 0.5061(5) 0.0916(11) Uani 1 1 d . . . . .
H15A H 0.692080 0.368598 0.421163 0.110 Uiso 1 1 calc R U . . .
H15B H 0.707132 0.370431 0.590466 0.110 Uiso 1 1 calc R U . . .
C16 C 0.75450(14) 0.2169(6) 0.4789(7) 0.1309(18) Uani 1 1 d . . . . .
H16A H 0.750516 0.161386 0.387480 0.196 Uiso 1 1 calc R U . . .
H16B H 0.761762 0.145641 0.558333 0.196 Uiso 1 1 calc R U . . .
H16C H 0.786291 0.287889 0.473275 0.196 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.413(3) . ?
O1 H1O 0.8200 . ?
O2 C3 1.415(2) . ?
O2 H2 0.8200 . ?
O3 C4 1.402(3) . ?
O3 H3 0.8200 . ?
O4 C5 1.235(2) . ?
N1 C5 1.331(2) . ?
N1 C1 1.4770(19) . ?
N1 H1 0.8600 . ?
C1 C4 1.528(2) . ?
C1 C3 1.529(2) . ?
C1 C2 1.530(2) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.514(2) . ?
C6 C7 1.514(3) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C7 C8 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 C10 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C10 C11 1.499(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.504(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.499(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.496(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.492(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.484(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1O 109.5 . . ?
C3 O2 H2 109.5 . . ?
C4 O3 H3 109.5 . . ?
C5 N1 C1 128.55(14) . . ?
C5 N1 H1 115.7 . . ?
C1 N1 H1 115.7 . . ?
N1 C1 C4 106.98(13) . . ?
N1 C1 C3 106.40(13) . . ?
C4 C1 C3 110.98(15) . . ?
N1 C1 C2 114.53(13) . . ?
C4 C1 C2 106.66(15) . . ?
C3 C1 C2 111.26(14) . . ?
O1 C2 C1 114.43(16) . . ?
O1 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
O1 C2 H2AB 108.7 . . ?
C1 C2 H2AB 108.7 . . ?
H2A C2 H2AB 107.6 . . ?
O2 C3 C1 112.66(15) . . ?
O2 C3 H3A 109.1 . . ?
C1 C3 H3A 109.1 . . ?
O2 C3 H3AB 109.1 . . ?
C1 C3 H3AB 109.1 . . ?
H3A C3 H3AB 107.8 . . ?
O3 C4 C1 110.93(17) . . ?
O3 C4 H4A 109.5 . . ?
C1 C4 H4A 109.5 . . ?
O3 C4 H4AB 109.5 . . ?
C1 C4 H4AB 109.5 . . ?
H4A C4 H4AB 108.0 . . ?
O4 C5 N1 124.39(15) . . ?
O4 C5 C6 119.46(15) . . ?
N1 C5 C6 116.09(14) . . ?
C7 C6 C5 111.55(15) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6AB 109.3 . . ?
C5 C6 H6AB 109.3 . . ?
H6A C6 H6AB 108.0 . . ?
C8 C7 C6 113.80(18) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7AB 108.8 . . ?
C6 C7 H7AB 108.8 . . ?
H7A C7 H7AB 107.7 . . ?
C9 C8 C7 114.53(19) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8AB 108.6 . . ?
C7 C8 H8AB 108.6 . . ?
H8A C8 H8AB 107.6 . . ?
C10 C9 C8 115.6(2) . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9AB 108.4 . . ?
C8 C9 H9AB 108.4 . . ?
H9A C9 H9AB 107.4 . . ?
C11 C10 C9 115.4(2) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 116.1(2) . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C11 115.5(2) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 116.6(2) . . ?
C14 C13 H13A 108.1 . . ?
C12 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C12 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C15 C14 C13 115.9(2) . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C13 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C14 116.4(3) . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
C14 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C4 153.18(18) . . . . ?
C5 N1 C1 C3 -88.1(2) . . . . ?
C5 N1 C1 C2 35.2(2) . . . . ?
N1 C1 C2 O1 -78.09(19) . . . . ?
C4 C1 C2 O1 163.76(15) . . . . ?
C3 C1 C2 O1 42.6(2) . . . . ?
N1 C1 C3 O2 -177.54(14) . . . . ?
C4 C1 C3 O2 -61.51(19) . . . . ?
C2 C1 C3 O2 57.1(2) . . . . ?
N1 C1 C4 O3 45.8(2) . . . . ?
C3 C1 C4 O3 -69.8(2) . . . . ?
C2 C1 C4 O3 168.82(17) . . . . ?
C1 N1 C5 O4 -7.4(3) . . . . ?
C1 N1 C5 C6 175.49(15) . . . . ?
O4 C5 C6 C7 -94.1(2) . . . . ?
N1 C5 C6 C7 83.2(2) . . . . ?
C5 C6 C7 C8 176.58(18) . . . . ?
C6 C7 C8 C9 178.6(2) . . . . ?
C7 C8 C9 C10 179.4(2) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C9 C10 C11 C12 179.5(3) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 178.9(3) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 178.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O4 0.82 1.86 2.593(2) 147.5 . yes
O2 H2 O1 0.82 1.91 2.703(2) 162.5 3_567 yes
O3 H3 O2 0.82 1.94 2.760(2) 177.8 3_566 yes
N1 H1 O3 0.86 2.26 2.680(2) 110.1 . yes
N1 H1 O4 0.86 2.29 3.003(2) 140.7 4_565 yes

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.058

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SPA246
_database_code_depnum_ccdc_archive 'CCDC 1831970'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        N14TM
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H37 N O4'
_chemical_formula_sum            'C18 H37 N O4'
_chemical_formula_weight         331.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0074 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.529(5)
_cell_length_b                   8.6680(17)
_cell_length_c                   9.0460(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.26(3)
_cell_angle_gamma                90
_cell_volume                     1998.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    288(2)
_cell_measurement_reflns_used    37316
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.056
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      288(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17599
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.744
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             5336
_reflns_number_gt                4264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1008P)²+0.1055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.108(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5336
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06410(3) 0.49864(11) 1.01490(8) 0.0529(2) Uani 1 1 d . . . . .
H1 H 0.087134 0.436535 1.040127 0.079 Uiso 1 1 calc R U . . .
O2 O 0.09092(5) 0.49460(15) 0.48613(9) 0.0745(4) Uani 1 1 d . . . . .
H2 H 0.066531 0.502446 0.423590 0.112 Uiso 1 1 calc R U . . .
O3 O -0.01560(2) 0.43521(10) 0.73494(8) 0.0411(2) Uani 1 1 d . . . . .
H3 H -0.023345 0.454495 0.819714 0.062 Uiso 1 1 calc R U . . .
O4 O 0.14769(3) 0.33300(9) 0.98943(7) 0.0420(2) Uani 1 1 d . . . . .
N1 N 0.12763(3) 0.37551(9) 0.74511(8) 0.02880(18) Uani 1 1 d . . . . .
H1N H 0.139052 0.359948 0.658743 0.035 Uiso 1 1 calc R U . . .
C1 C 0.07986(3) 0.47056(10) 0.74906(9) 0.02572(18) Uani 1 1 d . . . . .
C2 C 0.07776(4) 0.57518(11) 0.88478(10) 0.0363(2) Uani 1 1 d . . . . .
H2A H 0.111823 0.623227 0.903171 0.044 Uiso 1 1 calc R U . . .
H2AB H 0.052464 0.656669 0.862772 0.044 Uiso 1 1 calc R U . . .
C3 C 0.07902(4) 0.57669(13) 0.61350(11) 0.0428(3) Uani 1 1 d . . . . .
H3A H 0.044551 0.623106 0.598472 0.051 Uiso 1 1 calc R U . . .
H3AB H 0.104375 0.658957 0.630897 0.051 Uiso 1 1 calc R U . . .
C4 C 0.03348(3) 0.35858(11) 0.73865(11) 0.0349(2) Uani 1 1 d . . . . .
H4A H 0.035415 0.296579 0.649859 0.042 Uiso 1 1 calc R U . . .
H4AB H 0.035987 0.289515 0.823123 0.042 Uiso 1 1 calc R U . . .
C5 C 0.15552(3) 0.31033(10) 0.85779(9) 0.02658(19) Uani 1 1 d . . . . .
C6 C 0.20075(3) 0.20895(11) 0.81728(10) 0.0326(2) Uani 1 1 d . . . . .
H6A H 0.208886 0.136491 0.897023 0.039 Uiso 1 1 calc R U . . .
H6AB H 0.190493 0.150187 0.729081 0.039 Uiso 1 1 calc R U . . .
C7 C 0.24914(4) 0.30284(13) 0.78937(15) 0.0489(3) Uani 1 1 d . . . . .
H7A H 0.257875 0.366096 0.875731 0.059 Uiso 1 1 calc R U . . .
H7AB H 0.241181 0.371579 0.706509 0.059 Uiso 1 1 calc R U . . .
C8 C 0.29645(4) 0.20622(13) 0.75639(14) 0.0460(3) Uani 1 1 d . . . . .
H8A H 0.304725 0.139020 0.840224 0.055 Uiso 1 1 calc R U . . .
H8AB H 0.287322 0.141216 0.671514 0.055 Uiso 1 1 calc R U . . .
C9 C 0.34478(4) 0.29784(15) 0.72500(18) 0.0588(4) Uani 1 1 d . . . . .
H9A H 0.336437 0.364426 0.640754 0.071 Uiso 1 1 calc R U . . .
H9AB H 0.353543 0.363647 0.809545 0.071 Uiso 1 1 calc R U . . .
C10 C 0.39239(4) 0.20411(15) 0.69330(17) 0.0559(3) Uani 1 1 d . . . . .
H10A H 0.400776 0.137645 0.777604 0.067 Uiso 1 1 calc R U . . .
H10B H 0.383620 0.138186 0.608840 0.067 Uiso 1 1 calc R U . . .
C11 C 0.44042(4) 0.29536(15) 0.66186(18) 0.0601(4) Uani 1 1 d . . . . .
H11A H 0.449033 0.361559 0.746220 0.072 Uiso 1 1 calc R U . . .
H11B H 0.431974 0.361651 0.577460 0.072 Uiso 1 1 calc R U . . .
C12 C 0.48829(4) 0.20293(15) 0.63044(18) 0.0595(4) Uani 1 1 d . . . . .
H12A H 0.496779 0.136612 0.714797 0.071 Uiso 1 1 calc R U . . .
H12B H 0.479737 0.136805 0.545983 0.071 Uiso 1 1 calc R U . . .
C13 C 0.53623(4) 0.29502(15) 0.59917(18) 0.0599(4) Uani 1 1 d . . . . .
H13A H 0.527696 0.360805 0.514458 0.072 Uiso 1 1 calc R U . . .
H13B H 0.544485 0.361797 0.683335 0.072 Uiso 1 1 calc R U . . .
C14 C 0.58454(4) 0.20437(15) 0.56866(19) 0.0602(4) Uani 1 1 d . . . . .
H14A H 0.592928 0.137784 0.652884 0.072 Uiso 1 1 calc R U . . .
H14B H 0.576473 0.138485 0.483733 0.072 Uiso 1 1 calc R U . . .
C15 C 0.63220(5) 0.29712(16) 0.5393(2) 0.0635(4) Uani 1 1 d . . . . .
H15A H 0.623800 0.362567 0.454230 0.076 Uiso 1 1 calc R U . . .
H15B H 0.639724 0.364333 0.623550 0.076 Uiso 1 1 calc R U . . .
C16 C 0.68104(5) 0.20952(16) 0.5109(2) 0.0655(4) Uani 1 1 d . . . . .
H16A H 0.689184 0.142738 0.595164 0.079 Uiso 1 1 calc R U . . .
H16B H 0.673790 0.143738 0.425458 0.079 Uiso 1 1 calc R U . . .
C17 C 0.72845(6) 0.3031(2) 0.4844(3) 0.0885(6) Uani 1 1 d . . . . .
H17A H 0.720637 0.367026 0.397950 0.106 Uiso 1 1 calc R U . . .
H17B H 0.734795 0.371730 0.568183 0.106 Uiso 1 1 calc R U . . .
C18 C 0.77759(7) 0.2179(3) 0.4616(4) 0.1241(10) Uani 1 1 d . . . . .
H18A H 0.773280 0.156787 0.373192 0.186 Uiso 1 1 calc R U . . .
H18B H 0.785599 0.151632 0.544884 0.186 Uiso 1 1 calc R U . . .
H18C H 0.805754 0.289870 0.451877 0.186 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4120(13) . ?
O1 H1 0.8200 . ?
O2 C3 1.4021(15) . ?
O2 H2 0.8200 . ?
O3 C4 1.4167(11) . ?
O3 H3 0.8200 . ?
O4 C5 1.2344(11) . ?
N1 C5 1.3352(11) . ?
N1 C1 1.4738(10) . ?
N1 H1N 0.8600 . ?
C1 C2 1.5297(12) . ?
C1 C4 1.5299(12) . ?
C1 C3 1.5321(12) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.5127(11) . ?
C6 C7 1.5125(14) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C7 C8 1.5131(13) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 C9 1.5080(16) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 C10 1.5029(15) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C10 C11 1.4999(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5018(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.5015(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.5011(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.4947(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.4945(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.4875(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.480(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
C4 O3 H3 109.5 . . ?
C5 N1 C1 128.62(7) . . ?
C5 N1 H1N 115.7 . . ?
C1 N1 H1N 115.7 . . ?
N1 C1 C2 114.69(7) . . ?
N1 C1 C4 106.40(7) . . ?
C2 C1 C4 111.30(7) . . ?
N1 C1 C3 106.88(7) . . ?
C2 C1 C3 106.67(8) . . ?
C4 C1 C3 110.85(8) . . ?
O1 C2 C1 114.33(8) . . ?
O1 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
O1 C2 H2AB 108.7 . . ?
C1 C2 H2AB 108.7 . . ?
H2A C2 H2AB 107.6 . . ?
O2 C3 C1 111.05(9) . . ?
O2 C3 H3A 109.4 . . ?
C1 C3 H3A 109.4 . . ?
O2 C3 H3AB 109.4 . . ?
C1 C3 H3AB 109.4 . . ?
H3A C3 H3AB 108.0 . . ?
O3 C4 C1 112.60(8) . . ?
O3 C4 H4A 109.1 . . ?
C1 C4 H4A 109.1 . . ?
O3 C4 H4AB 109.1 . . ?
C1 C4 H4AB 109.1 . . ?
H4A C4 H4AB 107.8 . . ?
O4 C5 N1 124.09(8) . . ?
O4 C5 C6 119.60(8) . . ?
N1 C5 C6 116.25(7) . . ?
C7 C6 C5 111.71(8) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6AB 109.3 . . ?
C5 C6 H6AB 109.3 . . ?
H6A C6 H6AB 107.9 . . ?
C6 C7 C8 113.81(9) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7AB 108.8 . . ?
C8 C7 H7AB 108.8 . . ?
H7A C7 H7AB 107.7 . . ?
C9 C8 C7 114.61(10) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8AB 108.6 . . ?
C7 C8 H8AB 108.6 . . ?
H8A C8 H8AB 107.6 . . ?
C10 C9 C8 115.50(11) . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9AB 108.4 . . ?
C8 C9 H9AB 108.4 . . ?
H9A C9 H9AB 107.5 . . ?
C11 C10 C9 115.45(11) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 115.94(12) . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C11 115.64(12) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 116.32(12) . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C15 C14 C13 115.90(12) . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C13 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C14 116.92(12) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C15 116.43(13) . . ?
C17 C16 H16A 108.2 . . ?
C15 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
C15 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C16 117.01(15) . . ?
C18 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 35.06(12) . . . . ?
C5 N1 C1 C4 -88.44(10) . . . . ?
C5 N1 C1 C3 153.06(9) . . . . ?
N1 C1 C2 O1 -78.10(10) . . . . ?
C4 C1 C2 O1 42.75(10) . . . . ?
C3 C1 C2 O1 163.79(8) . . . . ?
N1 C1 C3 O2 45.48(11) . . . . ?
C2 C1 C3 O2 168.61(9) . . . . ?
C4 C1 C3 O2 -70.07(11) . . . . ?
N1 C1 C4 O3 -177.51(7) . . . . ?
C2 C1 C4 O3 56.90(10) . . . . ?
C3 C1 C4 O3 -61.67(10) . . . . ?
C1 N1 C5 O4 -7.26(15) . . . . ?
C1 N1 C5 C6 175.64(8) . . . . ?
O4 C5 C6 C7 -95.06(11) . . . . ?
N1 C5 C6 C7 82.17(10) . . . . ?
C5 C6 C7 C8 176.91(9) . . . . ?
C6 C7 C8 C9 178.75(11) . . . . ?
C7 C8 C9 C10 179.47(12) . . . . ?
C8 C9 C10 C11 179.91(13) . . . . ?
C9 C10 C11 C12 179.83(14) . . . . ?
C10 C11 C12 C13 -179.96(14) . . . . ?
C11 C12 C13 C14 179.56(14) . . . . ?
C12 C13 C14 C15 -179.37(15) . . . . ?
C13 C14 C15 C16 179.07(15) . . . . ?
C14 C15 C16 C17 -178.98(17) . . . . ?
C15 C16 C17 C18 177.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.82 1.87 2.5930(11) 146.9 . yes
O2 H2 O3 0.82 1.96 2.7623(14) 167.3 3_566 yes
O3 H3 O1 0.82 1.91 2.7021(12) 160.9 3_567 yes
N1 H1N O2 0.86 2.26 2.6800(12) 110.4 . yes
N1 H1N O4 0.86 2.29 3.0021(11) 140.7 4_565 yes

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.041

